


The Gang Leader

by halcyon1993



Series: The Kinky Adventures of a Wolf and His Boy [37]
Category: Teen Wolf (TV)
Genre: Alpha Derek Hale, Alpha/Beta/Omega Dynamics, Anal Fingering, Anal Sex, Barebacking, Bikers, Bottom Stiles Stilinski, Come Sharing, Coming Untouched, Deepthroating, Deputy Stiles Stilinski, Discrimination, First Meetings, Knotting, Large Cock, M/M, Mates Derek Hale/Stiles Stilinski, Mating Bites, Omega Stiles Stilinski, Oral Sex, Porn With Plot, Post-Coital Cuddling, Rimming, Self-Lubrication, Top Derek Hale, True Mates
Language: English
Status: Completed
Published: 2018-10-08
Updated: 2018-10-08
Packaged: 2019-07-28 06:25:07
Rating: Explicit
Warnings: No Archive Warnings Apply
Chapters: 1
Words: 8,528
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/16236017
Author URL: https://archiveofourown.org/users/halcyon1993/pseuds/halcyon1993
Summary: To prove to his sexist coworkers that his omega status doesn’t mean he can’t do his job, Deputy Stiles Stilinski infiltrates a gang of alphas in hopes of gathering intel on them. He quickly finds himself falling for the leader.





	The Gang Leader

**Author's Note:**

  * For [HinoteOokami](https://archiveofourown.org/users/HinoteOokami/gifts).



> As always with this series, don't judge me for the depravity I have written…

"You've got this. You can do this. You won't mess this up, and then they'll finally treat you with the respect you deserve."

Stiles gives himself his pep talk as he stands nervously outside of Knotheads, a biker bar that is infamous in his town. He thinks that the name is stupid, but apt. Within, the patrons of Knotheads are mostly alphas—gruff men who bring trouble with them wherever they go. There is little light outside, but Stiles can still see that the grimy parking lot is mostly filled with bikes, some scruffy and rundown and others that look meticulously cared for. This, combined with the raucous sounds he can hear coming from within the building itself, makes Stiles sure that his superiors had chosen the correct night for him to do this. Doesn't make it any easier, though.

For as long as he can remember, he has wanted to follow in his dad's footsteps and enter law enforcement. So far, though, it's been…difficult. There are discrimination laws in place to prevent his bosses from firing him because of his omega status, but that doesn't mean they like having him there.

Ever since he joined the force as a deputy, he has been right on the bottom of the ladder and looked down on by all of his alpha coworkers. Those who don't look down on him have never said anything to deter the others, so for a couple years now Stiles has been on his own, powering through all the snide comments and lewd remarks about his biology with only his best friend, Scott McCall, and Scott's mother, Melissa, to offer him support. He is getting tired of it, but it didn't stop him from accepting when the chief came to him last week with a proposal.

Stiles saw it as his last chance to prove himself to his naysayers, to prove that his omega status doesn't mean he can't be a good cop.

Failure is not an option.

And if he does fail…Stiles will cross that bridge if and when he comes to it.

After taking a deep breath, he pushes through the swinging doors that serve as the entrance to Knotheads and tries not to cough when the stench of cigar smoke clogs his nose. His eyes water, but he blinks the stinging away and walks through the gloom with his head down so as to not draw attention to himself. His main objective is to find the leader of the biker gang that frequents this lovely establishment, so before he does anything else, Stiles wants to sit silently and watch.

He makes it to the bar without incident, and a huge man wearing leather trousers, a leather vest and nothing else saunters over to him, his blue eyes narrowed. His beard is thick and blond, his short hair is messy and the scent coming off him is a mixture of smoke, sex and alpha musk that is difficult for Stiles to stomach. But he does.

"What can I get you?" the bartender asks him.

Wanting to look tough, Stiles orders some whiskey. The bartender scoffs, pours some amber-coloured liquid into a dirty tumbler and shoves it at him. "Enjoy," he sneers.

"Thanks," Stiles responds.

With his drink in hand, he turns around on his stool and observes his surroundings as subtly as he can.

All around him there are burly alpha men and a few women grouped together around circular tables or squished into booths. Some of them have smaller men and women hanging off of their arms—omegas—and most look like they're having a good time. There is alcohol and greasy fried food everywhere, the smell of it mixing with the smoke and the alpha pheromones that still linger in the air. Most of the alphas have some form of leather on their bodies, be it trousers and vests like the bartender or simply a leather jacket over a T-shirt. Every single one of the alpha men has facial hair, either stubble or a full-blown beard, and either muscles or a beer belly stretching out their shirts, whereas the alpha women are all beautiful, but it's a dangerous kind of beauty.

Every one of them looks like they could beat Stiles with ease if they got into a fight.

Great.

The omegas are very different, dressed either more conservatively or in barely anything at all. There's even a tiny thing to Stiles' left who sits in an alpha's lap in nothing but a thong. Not one of them looks like they don't want to be there. In fact, Stiles would say that, judging purely from the way they plaster themselves against the sides of the alphas with happy smiles on their lips, they are exactly where they want to be. He doesn't understand it at all; apart from his dad, there isn't an alpha he has met that he would want to be that close to.

Stiles sips his whiskey and tries not to wince as it burns going down his throat. It's not the first time he's had it—out of curiosity, and because he wanted to be feel older, he broke into his dad's liquor cabinet when he was just entering his teenage years and sampled some of the drinks within. The alcohol had made him cough, sputter and nearly throw up, it was so disgusting, and the noise had been what aroused his dad to what he was doing. He was grounded for weeks.

Now, though, Stiles grits his teeth and pushes through the nausea in his gut to take another sip. He has an appearance he wants to uphold, after all, and he still hasn't located the leader of this big group—if they're even here right now. That's something Stiles has to consider. In spite of his superiors' certainty that the leader would show his face in Knotheads tonight, Stiles can't see him anywhere. He has a vague description—around six feet tall, muscular, short dark hair, neat beard—but it matches several of the alphas currently in the bar, and none of them seem to radiate more than the typical arrogance that the vast majority of the alphas in Stiles' life possess.

Stiles tamps down his frustrations and has just raised his tumbler to take a third sip of his whiskey when the door swings open and someone steps through.

He freezes with his tumbler halfway up to his lips, because…wow.

The man matches the description to a T, and almost everyone in the place turns to look at him as he walks right up to the bar, mere feet from Stiles. There is respect in all of the other alphas' eyes.

This must be him. The leader.

He wears expensive shoes, a pair of black jeans, a blood-red henley with a low V-neck and a well-worn leather jacket on top. Dark chest hair peeks out of his shirt.

"Alright, Derek?" the bartender greets, his demeanour much more friendly now as he moves over to the leader.

Derek. Stiles stores the name away.

"Yup. Any trouble tonight?" Derek asks the bartender, his voice low and smooth. It sends a shiver down Stiles' spine.

 _What the hell?_ the omega thinks. A reaction like that isn't normal.

"None. Except…"

The bartender leans in close to Derek and drops his voice too much for Stiles to overhear. He realises that he has still been sitting there with his tumbler half-raised to his lips, and with a flush of embarrassment he brings it up the rest of the way and finally takes that third sip.

Both Derek and the bartender glance Stiles' way then. It's so quick that Stiles almost misses it, and in fact he isn't entirely sure it really happened. But then Derek pats the other alpha on the shoulder and turns around to face Stiles properly, their eyes locking, and Stiles is sure that he wasn't imagining things. He tenses up, afraid that he has blown his cover already. _I'd expect nothing less from an omega like you,_ someone says in Stiles' head. It's a combination of all the different condescending voices he has heard since he joined the police force. Like all those other times, instead of making Stiles feel bad about himself like the people who spoke those words probably intended, it just makes him more determined.

 _Act natural,_ he tells himself. _Derek doesn't know anything._

"Haven't seen you around here before," the alpha says, sliding closer so that he can sit down on the stool right next to Stiles'.

"Since I haven't been in here before, I don't doubt it," Stiles sasses. He is proud of himself for not stuttering.

If he had, he doesn't think anyone could really blame him—not with Derek staring at him so intensely. Derek is sex personified, with his powerful body, attractive face and smouldering gaze. He is everything an alpha should be—strong, handsome and giving off a musky, masculine scent that's all him and not because of cologne—but there's more to him too.

Derek isn't just the typical alpha, Stiles can tell that right away. There is something almost…soft…about him. His pretty hazel eyes aren't hard like Stiles had expected. But that can't be right. Everything Stiles had been told about the patrons of this bar and their leader painted a picture of absolute toughness and ruthlessness, of people who are uncaring about anything but themselves.

It could be an act, but as he ends up lost in Derek's eyes, Stiles doesn't know what to believe.

"You got a name?" Derek enquires, leaning his elbow on the bar.

Stiles gives it, forgetting entirely that he is supposed to be calling himself James while he is undercover. Shit.

"That's an unusual name," Derek comments. He runs his eyes up and down Stiles' body, not even attempting to hide his interest.

"It's a nickname."

At least Stiles has that going for him. His actual name isn't out there.

Derek's eyes gleam and his thin lips twist with amusement. "Secretive little thing, aren't you?"

"Something like that. You wouldn't be able to pronounce my real name anyway, so really I'm doing you a favour."

"Is that right?"

"Yes."

"Well, I guess a thank you is in order, isn't it?"

Stiles wonders what the hell is happening. This wasn't the plan. He was just supposed to get in, identify the leader, gather some more intel and leave. He wasn't supposed to flirt—and yet he can't stop himself. Something about Derek is just irresistible. Although, after he mulls it over a bit more, he decides that maybe flirting is still a good way to gather intel.

"I guess so," he answers, downing the last of his whiskey.

Derek's gaze leaves his then, and Stiles feels like he can breathe for the first time in minutes. "Devon, can I get a refill for my new… _friend_ …here?" the alpha asks the bartender.

"You got it, boss," Devon assents. He tips the neck of a nearly empty bottle over Stiles' tumbler, draining the last of the whiskey out into it. "Enjoy," he tells Stiles with a conspiratorial smile. Stiles wonders what that's about.

"Don't mind him," Derek says, noticing his confusion. "He's a good guy, but a bit of a tease. Likes to push the boundaries."

"And you don't?" Stiles asks.

Derek regards him closely, his eyes becoming more heated. "I don't know. Do you want me to push them?"

His mouth dropping open, all Stiles can do is sit there like an idiot as the seconds tick by and Derek's smile widens into a full-blown grin. His face must be red as hell by now, and it doesn't help that he can feel the beginnings of slick leaking from his hole, soaking into the soft material of his yellow boxer-briefs. If Stiles hopes that the other smells in the bar will mask the scent of his inappropriate arousal, he is disappointed. Derek looks down at his crotch and his grin gets this predatory aspect to it, like he is a wolf closing in on his prey.

Stiles doesn't like feeling like prey. Or at least that's what he tells himself. As he snaps his mouth closed, he knows he is only lying to himself.

"I thought so," Derek says after a while. He rises from his seat and looks back at Stiles over his shoulder as he walks away. "If you want to, come with me."

Before he can think better of it, Stiles drinks all of his refill in one go, nearly vomits, and then leaps up from his stool to chase after Derek. What is he getting himself into? He should not be doing this. Every rational part of Stiles' brain knows this, but unfortunately none of them are online right now. Pure animal lust has taken over, and Stiles is powerless to resist the compulsion to roll over and show Derek his belly. God help him, he wants the alpha so fucking badly. He wishes he could blame it on him not getting any action in months, but he is sure that, even if he'd been fucked that very morning, he'd be just as desperate for Derek to ravage him again tonight.

He's totally going to get fired tomorrow.

And most of him doesn't care anymore.

* * *

Derek walks through a door in the back of the bar and enters a hallway. He can hear the omega following behind him, so he doesn't stop as he walks over to the staircase at the end of the hall and ascends it to the red door at the top. After unlocking it, he steps through it and into what doubles as storage for the bar downstairs and a shabby little apartment which any of his guys can use to sleep off their drink if they get too wasted on any given night. Derek has a rule that no one is to bring their mates or conquests here, and they all know better than to betray his trust.

But tonight, he intends for him and Stiles to break that rule.

"What is this place?" the omega asks, stepping nervously in behind him.

Derek explains as he shuts and locks the door again, and then he says, "I thought it would give us some good privacy."

"P-privacy for what?"

Derek smirks at Stiles. He's so cute.

That had been Derek's first thought when he laid eyes on him back down at the bar. He has been attracted to omegas before, of course, but Stiles was so clearly out of place there and trying to act like he wasn't. It was both endearing and suspicious. His initial thought had been that Stiles was a thrill-seeker who'd been looking to sleep with a big, bad alpha to get his rocks off, and Derek wouldn't have minded being that alpha.

But then Devon had told him the truth.

Stiles is a cop.

Devon is Derek's righthand man as well as the bartender of Knotheads, and part of his job is to know at least a little about everyone who works with or for the police department and inform Derek if anyone comes sniffing around. It's just smart business, especially because some of his boys have a penchant for flirting with the law every now and then. Stiles Stilinski—son of a prominent cop—was a minor blip on Devon's radar, so small that he didn't think the omega ever saw any action. He figured he was just bad enough at his job to be figuratively benched but not enough to actually be fired. Apparently Stiles has been taken off the bench now.

So Derek had two motives for inviting Stiles up to this apartment-slash-storage-area: to get him away from his boys before he could find whatever he was obviously sent into Knotheads for, and to have a little fun with him before he sends him on his way. Sue him. Derek hasn't got laid in a while, and while Stiles is a cop and getting involved with him is probably something that should go against Derek's better judgment, the omega is damned sexy. With his pretty eyes that matched the whiskey he was struggling to drink, and his pale, mole-dotted skin that looked like it would mark up so easily.

How on earth was Derek supposed to resist?

Especially after he noticed Stiles regarding him back with ill-disguised interest.

"I think you know what we need privacy for," Derek says. He grabs Stiles' hand and drags him over to where a double bed is pushed up against a wall next to some boxes of unopened liquor bottles.

"Oh…"

"Having second thoughts?"

Stiles hesitates, which means that yes, he is, but then he seems to come to a decision. He shakes his head. "No. I want this."

"Good." Derek grins. "I'm gonna rock your world."

"Oh my God!" Stiles' whole body shakes as he holds back laughter. "I can't believe you just said that! Are you ancient? No one says that anymore."

Derek rolls his eyes. "Whatever. Let's just get down to it, hmm?"

He tugs Stiles forward so that they are chest to chest and Stiles has to tilt his head up to keep looking him in the eye. All mirth is gone from his face, replaced by desire.

"What're you gonna do?" Stiles asks him. His Adam's apple bobs.

"If I told you, it would only ruin the surprise."

"Well…we wouldn't want that now, would we?"

"Definitely not."

Derek stares down into Stiles' lust-blown eyes for a few more seconds before crashing their mouths together. There's nothing gentle about the kiss. It's rough and demanding, Derek instantly taking control of Stiles and demanding that he submit. Stiles puts up an admirable fight but then gives in, sagging against Derek's body and digging his short nails into the alpha's shoulders hard enough for him to feel it through the leather of his jacket. Derek keeps one hand curled almost possessively around the back of Stiles' neck, holding him in place, while he travels the other down the length of Stiles' back until he cups his round cheeks, causing the omega to moan loudly into his mouth.

After a while, Stiles ends the kiss and breathes deeply to take in some fresh oxygen. "Please," he begs, shoving his ass back into Derek's hand.

His cock as hard as stone, Derek picks Stiles up, spins around and throws him down on the bed before climbing on top of him. He is quick about getting the omega out of his clothes, needing to see and feel his naked skin. When Stiles' hideous yellow underwear is gone, Derek rises up on his knees and runs his gaze over every inch of his prize.

Stiles is toned and slender, the perfect omega body. His chest is smooth and his nipples hard and perky. Beneath his navel, a thin trail of fine brown hair runs down over barely developed abs before it meets the coarse curls surrounding Stiles' little omega cock. It strains up hard and needy, reasonably thick and at a length that Derek guesses is around four or five inches. Not too shabby for an omega. When he'd thought to bring Stiles up here, he'd had a plan—to bury himself so far inside Stiles that he'd feel his cock in his throat, and then he'd send him on his way without whatever it was he was sent into Knotheads to find. But the sight of the omega lying beneath him, looking all sweet and blushing, has Derek's mind changing.

Instead of divesting himself of his own clothes, he just gets rid of his jacket and then positions himself between Stiles' legs.

"Hold on for the ride," he warns the cop.

"What?"

Derek meets his eyes, winks, and then descends on his cock with enthusiasm.

He is no stranger to giving blowjobs. Some male alphas shy away from such things, thinking it beneath them and that if a cock is going to get sucked, it should be theirs.

Derek isn't one of those alphas.

He was raised to respect everyone, as long as they respected him, and part of the respect he shows is to make sure whoever he has in his bed—or the bed above Knotheads, in this case—experiences pleasures of all kinds and isn't just some hole for him to use to get himself off. He wishes other alphas had similar mentalities, but change is sadly slow, and there are still many who oppose the omega rights movement and see them as second-class citizens. The only good thing is that, to Derek, watching how someone treats an omega is a reliable way to measure their worth as a person. He has used it to ensure that everyone he welcomes into his little family of rambunctious misfits is a decent human being. Flirtations with the law aside.

Derek puts his all into the blowjob. Because of its size, he is able to fit all of Stiles' cock in his mouth at once without triggering his gag reflex, burying his nose in the curls at the base. He breathes in the scent of him and is quickly addicted. It's sweet and heady and better than any omega scent he has smelled in a long time.

While he bobs his head up and down, Derek slips his right hand between Stiles' legs to fondle his balls and then explores further back, over Stiles' perineum and into the shadowed crack between his smooth cheeks. The omega whines and spreads his legs even wider to accommodate him, which he appreciates. He rewards such good behaviour by rubbing his index finger in circles over the tight rim of Stiles' hole, gathering some of the slick dripping from it and using it to ease his way inside. Heat surrounds his finger, and Stiles' inner walls feel heavenly, like the finest silk.

While he continues to suck him off and slide his finger deeper inside his body, searching for his prostate, Derek peers up the length of Stiles' body and meets his wide-eyed gaze with a smug one of his own. Stiles' face is delightfully flushed, and as he stares, the red spreads down the omega's neck, over his collarbones and to his thin chest.

When, finally, Derek locates Stiles' prostate and brushes the pad of his finger over it, Stiles bucks up into his mouth and throws his head back on a bitten-off scream. He's beautiful to look at, like a living work of art. Before he can think better of it, Derek finds his mind drifting, fantasies filling it—them doing this on his own bed, him tying Stiles to it so that he is at his beck and call 24/7. It's such a caveman thought that Derek would never speak it aloud, but there is nothing to stop him from enjoying it in his head. There's also nothing to stop him from taking it one step further, of imagining tying Stiles to _him_ and not the bed, of sinking his teeth into the vulnerable stretch of skin between the omega's neck and shoulder to lay his claim for everyone to see.

He has never considered actually taking a mate before. What's so different about Stiles that the thought enters his brain now? Derek doesn't have the answer, so he mentally shrugs off any concern and just embraces it. He doesn't understand it, doesn't get why everything in him is suddenly telling him that Stiles is his, and maybe that's okay.

Maybe he doesn't need to get it.

Maybe all he needs to do is live in the moment and follow what his instincts are telling him.

Satisfied with his decision, Derek concentrates on providing Stiles with as much pleasure as he can muster. There would be no way for him to make a reality out of the future he just saw in his mind's eye if he doesn't prove to Stiles that he can be a good lover, is there? And he'll have to do something about the omega's vocation. He can't very well have his future mate and his found family being at odds with each other now, can he? Once he has made Stiles come, he'll have to figure out a way to make Stiles see that his people aren't bad. They just get a bit too enthusiastic from time to time and end up drawing the wrong sort of attention.

Should be easy, right?

Right.

After inserting a second finger into Stiles' welcoming body, Derek redoubles his efforts. He rubs relentlessly over the omega's prostate and pays special attention to the glans of his cock with his tongue.

Soon, Derek feels Stiles' orgasm approaching. His inner alpha is impatient to taste his future mate's seed, and Derek himself is no different. He is immensely glad when, with one last flick of his tongue over Stiles' slit, the omega tenses up atop the rumpled sheets and shoots his load right into Derek's mouth. It's thin and doesn't serve a biological purpose like an alpha's seed would, but that doesn't matter. To Derek, it's still delicious, and he savours it as it fills his mouth.

Once Stiles' orgasm has ended, Derek removes his fingers from the omega's hole, swallows half of his load and crawls up over him. His fingers still coated in slick, he runs them over Stiles' bottom lip to wordlessly ask him to open up, and then he kisses him again. He pushes Stiles' own come into his mouth and then just spends a while swapping it back and forth. Only when Stiles swallows it does Derek break the kiss to look down at him, his emotions an unfamiliar mixture of possessiveness and affection.

He still can't figure out why, but he likes it a lot and doesn't want it to end.

For now, though, it has to.

"That was…" Stiles says softly, lying boneless beneath Derek.

"Yeah," the alpha agrees, smiling.

"What about you?"

Derek's cock is still hard in his jeans, but he pays it no mind. He shakes his head. "Don't worry about me. That was just for you."

"Oh…"

"Maybe next time, though."

"Next time?"

Derek winks again. "If you're amenable."

Stiles blinks a few times and then nods jerkily. "I am."

"Great."

Derek kisses Stiles once more, chastely this time, and gets up from the bed. He retrieves Stiles' clothes from where he'd thrown them on the floor earlier and gives them back to their owner so that he can get dressed. As he does so, Derek is saddened by all the pale skin being covered up, but he knows he'll see it again. Hopefully soon.

"So…what now?" Stiles asks him when he is fully dressed.

"I have to tell you something," Derek says, standing in front of the door that leads back down into Knotheads.

"What?"

Derek can hear the nerves in Stiles' voice and rips the Band-Aid off. "I know who you are."

The omega's mouth drops open before he covers his shock. "And who am I?" he deflects, his guard going up.

"You work for the police. I'm guessing you were sent here to spy on us."

"And if I was?"

"Then I'd ask you if you're sure you knew what you were doing."

"What about you? Do you know what you were doing? If you knew who I was this whole time, then what was all that about?"

"I wanted to show you a good time so you'd see we're not bad people," Derek answers calmly. It's the truth. "And so you'd be open to being around me again."

"I…I don't understand," Stiles admits, frowning.

"I know the reputation some of my guys have given us, but I can assure you it's wrong. Have things gotten out of hand a few times? Yes, absolutely. But I stepped in before things could get worse and put my guys back in line. Every time."

"So what? You're the good guys?" Stiles asks incredulously.

"We're definitely not the bad guys."

"And who is?"

Derek recalls the interactions he has had with a few select members of the police force in the past. "I think that's something you _do_ understand."

"My bosses?"

"See? You didn't even have to think about it."

"They're a bunch of bigoted assholes, but they're not…criminals."

The argument is weak, and both of them know it. "We're not bigoted."

Stiles scoffs and crosses his arms. "Oh yeah?"

"Yeah. If you spent more time with me—and with my guys—you'd see that we treat everyone equally."

"Even a lowly omega like me?"

"You're not lowly," Derek corrects, such self-doubt not sitting well with him. "I've only known you an hour and even I can see that. Anyone who can't is a fool."

"Guess my bosses are all fools then."

Derek takes a step closer. "Then why do you still work for them?"

"Because it's what I've wanted to do since I was a kid. My dad was a cop and he was always my hero. I wanted to follow in his footsteps, but…"

Hearing the dejectedness in Stiles' voice, Derek closes the rest of the distance he put between them and hugs the omega to him. Stiles doesn't hug him back, but he doesn't pull away either, so Derek counts it as a win. "That's sweet, but if you're unhappy—if it's not everything you wanted it to be—then I think you should hand in your badge and quit. You don't seem happy."

Stiles doesn't respond, so Derek hugs him tighter and rests his chin atop his head. "Just think about it. Please?" he entreaties.

When Stiles nods, Derek finally releases him.

"I should go," the omega whispers.

"Come back anytime. I'll let my guys know that you won't mean them any harm."

"Thanks…"

With much reluctance, Derek unlocks the door and leads Stiles back down into the bar. While they were getting busy upstairs, most of his guys had gone back to their homes, leaving just Devon behind the bar and a couple stragglers in one of the booths. Closer inspection reveals that it's Boyd and his omega mate, Erica, and for once they aren't busy sucking each other's faces off. Derek catches their attention and waves them over. They come willingly, curiosity appearing on their faces when they see Stiles trying to hide behind him.

"Guys, I'd like you to meet someone," Derek says, stepping aside so that Stiles is in full view. He makes introductions and is pleased when Erica takes it from there.

"So, you're the one I saw the boss sneaking upstairs with," she says teasingly, her red lips pulled into a mischievous grin. "Nice catch."

Stiles is startled by her forwardness, but Derek is just amused. He's used to Erica by now.

"Uhh…thank you?" Stiles squeaks.

"You're welcome."

A few moments of uncomfortable silence pass—uncomfortable for Derek and Stiles, at least—and then Stiles sniffs the air. "You're an omega."

"Yup," Erica confirms proudly, her blonde hair bouncing.

"And you like it in here? At Knotheads?"

"Oh, hell yeah! I love it. Boyd and I come here all the time to get our drink on. Right, babe?"

Boyd, tall and dark, says nothing. He nods instead, stolid as ever.

"Ooh!" Erica exclaims suddenly, reaching out and snagging Stiles' wrist. "We should totally hang out sometime! I could give you all the dirt on the Bossman over there."

Derek growls but doesn't mean it. "Erica…"

The blonde just laughs. "Don't get your panties in a bunch," she tells him, then focuses back on Stiles. "So? What do you say?"

Stiles glances warily at Derek before responding with a simple, "Sure."

"Awesome! Here's my phone." Erica proffers a beat-up iPhone 5S. "Put your number in here and we'll set something up."

Derek watches approvingly as Stiles does as he has been told. While he can think of a few other omegas who would probably be better choices to ease Stiles into their family, Erica is still a good one. He just prays she doesn't scare him off instead.

When Stiles has handed Erica back her phone, she and Boyd bid him and Derek goodnight and leave the bar.

"She seems…nice," Stiles says once the couple is gone.

"She's a handful, but yeah, she's a good person."

"Like you said."

"Like I said."

"Right, well, I'm gonna take off too, I guess. Tonight was a bust anyway."

Derek would prefer it if Stiles didn't leave, but he says nothing to stop him as he walks with him to the exit. "Remember what I said," he murmurs.

"I will. I shouldn't, but something in me is telling me to trust you," Stiles reveals, his expression adorably confused.

"I'll be looking forward to the next time we see each other, then."

"Yeah."

With one last look, Stiles steps out of the bar and leaves Derek alone with just Devon for company. Before tonight, Derek wouldn't have minded—the bartender is good company—but now…all he wants is for Stiles to walk back through the door.

"Damn, you've got it bad, boss," Devon points out from behind the bar. "Never seen someone get under your skin that fast."

"That's because no one has before."

"I can't wait to tell your sisters about this, just you wait."

Spinning around, Derek aims a glare at his friend. He knows the shit they'd give him—especially Laura. "Don't you dare!"

* * *

"So, did you find him?"

Stiles raises his head from where he'd been looking at his desk and finds Chief Hudson standing on the other side, one eyebrow raised impatiently.

"Huh?" Stiles says stupidly, his mind not catching up.

Hudson sighs and shakes his head as if interacting with Stiles isn't worth the effort. When he speaks again, his words are slow and overly enunciated, like how some foreigners speak to natives whenever they go to another country, as if that will somehow bridge whatever language barrier is present. "Did you find the leader at Knotheads?"

Caught up, Stiles opens his mouth to say that yes, he did, but what comes out is, "No."

Hudson's lips settle into a tight line of disapproval. "Typical," he says under his breath. Stiles flinches.

"I'm sorry, but—"

"I don't want to hear it. I should've known better than to send an omega in there, but there was no one else I wanted to risk. Forget about it."

Stiles watches helplessly as Hudson walks away from his desk and converses with a couple other deputies, both alphas. The deputies look his way and smirk at him before returning their attention to Hudson, all while Stiles mulls over what just occurred. Why didn't he tell Hudson the truth? Not the whole truth, because there was no way telling the chief that he'd got a blowjob from Derek would have gone over well, but he _had_ found Derek and spent enough time around him that he and the station's best sketch artist could come up with something good.

So what stopped him? Stiles isn't sure, but the possible answers frighten him.

And what had Hudson meant by that last comment? There was no one else he wanted to risk sending into Knotheads, he'd said. Stiles curls his hands into fists on his knees as he gets stuck on the chief's words. Hudson had suspected there would be a risk of something bad happening to whoever he sent into that bar, and he'd chosen Stiles because he is an omega and is therefore expendable.

Just when Stiles didn't believe he could hate where his lifelong dream has taken him any more than he already did. He barely knows the guy, but he is starting to suspect that Derek was right.

Getting up and walking to the break room to get some coffee, Stiles just holds back from doing something reckless, like turning in his badge then and there like Derek had suggested. As mad as he is right now, Stiles can't make such a big decision on a whim. He needs to sleep on it. Tomorrow, if he still feels the same, if he still doesn't believe he can continue to work in an environment that is so openly hostile toward him…he'll do it.

And then he'll go back to Knotheads and tell Derek.

The thought sends a thrill down Stiles' spine. Already he wants to return to the bar and fall right into bed with Derek. The way the alpha had touched him… Stiles has had a lover or two in the past who were good to him, but their touch hadn't sent him flying as high as Derek's had, and they hadn't even had full-on sex.

"Fuck," he breathes, having to adjust himself in his jeans. He wants it again.

Desperately.

* * *

Two nights later, Derek spends most of his time with his eyes glued to the entrance to Knotheads, waiting on bated breath for Stiles to walk through the door and grace him with his presence again. It's pathetic. As far as he knows, the omega hasn't even got into contact with Erica yet, so that he'd come back to the bar just to see Derek is a fool's dream. And Derek is apparently a fool, because he can't remove his gaze from the entrance.

It's two hours into his lonely vigil that he appears.

Stiles.

Derek perks up instantly and marches over to him before he even has the thought. "You're back," he says when they are next to each other.

Stiles peers up at him and smiles shyly. "Yeah, I'm back. Hi."

"Hi," Derek echoes.

"So, that offer to hang out with you guys…does it still stand?"

Derek nods eagerly. If he had a tail, it would be wagging quickly behind him. "It does."

"Then I'd like to take you up on it. If that's alright."

"What about your job?" Derek enquires.

Stiles breaks eye contact for a moment, a shadow of displeasure flitting across his stunning features. "I don't work there anymore. You were right. I deserve better than how I was being treated."

"You really do."

 _You deserve everything,_ Derek thinks, and then he wonders where the thought came from.

"This is all a bit intimidating," Stiles says, casting a wary look around the bar. "I mean, where do I start?"

Getting over the thought he'd had that was way too soon, Derek drapes his arm across Stiles' shoulders and leads him further into the bar. "Don't worry; I'll take care of you."

* * *

When the night is over and the bar has closed, Derek sits behind the wheel of his Camaro and drives Stiles back to his place. The evening had gone surprisingly well. Stiles was cautious at first. It was obvious that he was still second-guessing his choice to put his trust in what Derek had said about the gang being comprised of good people, but with Derek there to smooth any awkwardness away, he'd eventually started to open up and hit it off with a bunch of them, alphas and omegas alike.

He fit right in, and Derek couldn't be prouder.

When they reach their destination, he turns off the engine and gets out of his car. He walks around and opens Stiles' door for him too.

"Thanks," the omega says, blushing.

"You're welcome."

"Nice place."

Derek flicks his eyes over the bungalow and grunts. "It's okay."

Stiles chuckles after a few seconds of silence. "Are you gonna show me the inside or are we just gonna stand here?"

With an unattractive snort, Derek grabs Stiles' hand and walks him up the path to the front door. Once they've entered and the door is locked again behind them, he bypasses the living room and the kitchen and heads straight for the hallway in the back. He goes past the bathroom and the linen closet and doesn't stop until they reach the door to his bedroom, which is pushed to so that Stiles can't see inside just yet. Before he opens the door, he spins around, places his hands on Stiles' shoulders and looks straight into his whiskey-coloured eyes.

"If you don't want this, tell me now," he says. "And be sure, because once we go in there, I don't think I'm gonna be able to stop myself if you change your mind."

Stiles steps closer and brazenly cups Derek through his jeans. "Good."

Emboldened by the omega's actions, Derek shoves his bedroom door open so hard that it rebounds off the wall and he has to open it all over again. He drags Stiles through the doorway and kicks the door shut so that he doesn't have to worry about it anymore, and then the two of them fall onto his king-size bed. He made it that morning, getting out as many wrinkles as he could in his red bedsheets, but his work is ruined as he rolls them so that Stiles is on his back beneath him and he can wedge himself between the omega's legs, grinding their erections together.

"Off!" Stiles gasps, already panting and needy. "Get naked. You fucking suck for not letting me see you last time."

Derek laughs. "Sorry."

"You can make it up to me by getting your ass naked right now, Mister."

"Yes, Sir."

* * *

Stiles watches raptly as Derek's weight disappears from atop him and the alpha gets up from the bed to stand beside it instead. First to go is Derek's leather jacket, and it's the only article of clothing that he treats with any care once it's off. He drapes it over the back of a desk chair and then one by one strips out of the rest of his garments. He makes it slow and sensual, not like a strip tease but still giving a show to the omega on his bed.

Stiles licks his lips when Derek grabs the hem of his grey henley and peels it from his torso. Derek's body is tanned and muscular, his chest broad and hairy. Stiles already knew this, but he still isn't prepared for the full effect of seeing the alpha topless. The reality is even more amazing than the fantasies he'd had when he was in his own bed the night after Derek blew him, when he'd got hard again and jerked off to thoughts of having Derek there with him, touching him and letting himself be touched in return. That those fantasies might come true in mere seconds is almost too much.

Next, Derek toes off his shoes, pulls off his socks and then moves his hands to the button and zipper of his jeans. With them both undone, he pushes the rough fabric down his thick legs and kicks the offending garment aside, leaving him in just a pair of black boxer-briefs that are tight enough to leave absolutely nothing to the imagination. Already Derek's big alpha cock strains to get free of the fabric, and after standing there just long enough to make Stiles antsy, Derek removes his underwear, leaving himself completely naked.

Just the sight of him was worth the wait. Derek's cock is long and thick, the fat head still partially hidden by foreskin as pre-come beads at the slit.

Stiles wants to choke on him.

"Come here," he says, his voice low with need.

Derek gets onto the bed again, but instead of giving Stiles what he wants, he tugs at Stiles' clothes as well. The omega huffs but allows it.

"Just as beautiful as I remembered," Derek compliments him when they're both naked.

Stiles can feel his face heat up and can't meet the alpha's gaze. He doesn't like feeling like a weak, demure little thing right now, so while he appreciates that Derek approves of how he looks, he waves off his words and pushes at him to get him to turn over onto his back. From the expression on Derek's face, he knows exactly what Stiles intends to do next, which only makes Stiles want to do a good enough job of it to wipe that smug look away. It's a good look on Derek—anything would be, his face is so stupidly perfect—but Stiles thinks the alpha would look even better gasping and scrunching his features up in pleasure as Stiles deep-throats his impressive cock.

So that's exactly what he does.

Not wasting any time, Stiles forces his way between Derek's hairy legs and without preamble takes his massive cock as far as he can in his mouth. He's given enough blowjobs in the past that he thinks he is pretty damn good at them, but never has he blown someone of Derek's size. He isn't used to the extra couple inches, so it takes him a while of bobbing his head up and down for his throat to acclimate and accept the head of Derek's cock. By the time he has done it, his eyes sting with unshed tears and his hands grip Derek's hips hard enough to bruise, but he is too satisfied with himself to care. The sharp gasps and moans that pour from the alpha's lips don't hurt, either.

"God…Stiles!" Derek cries out when the omega manages to take him in all the way.

Stiles hums, pulls off long enough to take a breath and then dives right back on that gorgeous cock. He buries his nose in the dark curls at the base, just like Derek had done to him, and stays there as long as he can, inhaling the masculine scent of his sex. When his throat protests and he can't put off breathing any longer, he reluctantly lets Derek's cock slip from his mouth and wipes the moisture away from his eyes.

"Damn, you're good at that," Derek says, pulling him up into a short kiss.

"Thanks."

"Gotta get inside you."

Stiles' eyelids flutter. "Hell yes."

His world blurs as Derek reverses their positions, and then he finds himself doing an imitation of a pretzel as Derek shoves his legs back so that his knees meet his chest and his dripping hole is exposed.

"So hot…" he hears Derek mumble, right before that wicked mouth starts eating him out.

Stiles fists his hands in the sheets and holds on as Derek licks around his slick rim and wiggles the tip of his tongue inside. Derek is apparently a fucking _king_ at rimming, so much so that Stiles has to fight off jealous thoughts about how he got so talented. It's actually pretty easy, because Derek seals his lips around his hole and sucks on it at the exact same moment he slides his tongue in as deep as he can get it. Then Stiles has no space in his brain for jealousy. He almost comes, it feels so fucking good.

Soon enough, a finger joins Derek's tongue. Then two. Then three.

When Derek finally lets Stiles' body uncurl, his hole is stretched and ready, and the alpha's dark beard his slathered with clear slick.

"Gonna fuck you…" Derek promises as he rubs the head of his cock over Stiles' hole.

"Please. Want you."

"How bad?"

Stiles whimpers and wraps his legs around Derek's hips in an effort to pull him inside, but it doesn't work. "Really fucking bad. Please!"

Derek shushes him and presses their lips together, getting slick on Stiles' face too. "I've got you."

When Derek pushes the head of his cock inside, Stiles closes his eyes and just focuses on the feeling of being slowly filled up. It's more than he has ever taken, bigger than even his biggest dildo, but he wouldn't change a thing about it. He wants all nine inches of Derek inside him, for Derek to use them to ruin him for anyone else and then knot him up good and tight and pump him full of his seed.

Derek must be reading his mind because, as he bottoms out, he promises to do just that.

Once Stiles has given him the go-ahead a minute later, the alpha withdraws most of his cock and then fucks back inside, starting up a reasonably fast pace. Stiles arches his back and clutches at Derek's broad shoulders, powerless to silence the needy noises he is making. They only seem to spur Derek to go faster, and before Stiles knows it he is being fucked within an inch of his life. Derek leans down over him and noses beneath his jaw, kissing and nipping at the pale skin to mark him up. In the tiny part of Stiles' mind that isn't rendered incapable of thought by the relentless assault on his prostate, he knows he will cherish every bruise and bite mark.

After an indeterminate amount of time—it could be five minutes or five hours, for all Stiles knows—he feels the familiar tingle in his gut that speaks of his impending orgasm. He warns Derek and scratches his nails down Derek's back when the alpha bites his neck harder and his thrusts get impossibly quicker, his heavy balls smacking against the top of Stiles' ass cheeks.

"Come for me," the alpha whispers right into his ear.

That's all she wrote.

Stiles yells as he shoots between them, smearing their bellies with his come. He thinks he blacks out for a few seconds, because one moment Derek is thrusting into him, and the next he feels Derek's knot locked in place inside him, thick seed warming his guts and a bright flash of pain on the side of his neck. Stiles pants as both the pain and the pleasure dissipate and he comes back down. He is docile when Derek switches their positions yet again so that he is lying stretched out atop him and he can tuck his face into Derek's sweaty neck. There's nowhere else he would rather be.

"Mate," Derek says, so quietly that Stiles almost doesn't hear him.

"Hmm?" he asks, too worn out to use proper words.

"We're mates. True mates… Can't you feel it?"

Blinking sluggishly, Stiles looks inside of himself and… _there_. He can feel a second presence in his chest, a tether between him and Derek. That explains the pain he'd felt. Derek bit him. Claimed him.

"Wow," he says.

"Mine," Derek growls possessively, wrapping him up tight in his arms.

Stiles should probably protest. That haven't even known each other a week and they have already mated. Sure, it's fate. They're true mates, which explains the inexorable draw he'd felt toward Derek from the moment they met, but it still seems incredibly fast for him to be okay with it. And yet he is. Maybe it's just the afterglow, but he feels warm and safe in Derek's arms, and something tells him that he can trust the alpha with his heart.

He isn't sure what's going to happen next. He is still out of a job, Derek is still the leader of what is essentially a biker gang, and he doesn't even want to think about introducing Derek to his dad.

All Stiles knows is that, as they get to know each other properly, they'll figure it all out together.

**Author's Note:**

> And I'm back with a longer fic again! Some plot snuck into this one. Hope you guys don't mind. :P There is quite a bit of insta-love here, but I honestly didn't feel like dragging out the Sterek relationship in this work and just wanted to get right to the good stuff. It was also a conscious choice not to include any more scenes outside of that—e.g. Stiles quitting—because I wanted to focus as much as I could get away with on Sterek and on nothing else. As a consequence, there is a lot of telling and not much showing, but as this is just meant to be a fun little thing, I don't feel too bad about it. Anyway, I'd like to say a huge thank you to HinoteOokami for giving me this prompt. I hope it was everything you wanted it to be. :)
> 
> Stay tuned for my next PWP, in which Stiles is pulled over for speeding by Deputy Hale. Not wanting his dad to find out, he offers to give the deputy anything if he rips up the ticket. Derek takes Stiles' tight little ass. Top!Derek/bottom!Stiles.
> 
> To see what else is coming up soon, check my list [here](https://archiveofourown.org/series/887604). I'll be keeping it up to date.
> 
> **P.S. Don't forget to subscribe to me to be notified when my future fics go live, which will all be Sterek. And please check out my past fics if you haven't already and are interested.**


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